Authors Verma, N; Tu, Z; Lu, MS; Liu, SH; Renata, S; Phang, RP; Liu, PK; Ghosh, B; Lin, CH in AMER CHEMICAL SOC published article about MANNAN-BINDING PROTEIN; ONE-POT SYNTHESIS; AGLYCON TRANSFER; ACID; LACTOSYLCERAMIDES; SACCHARIDES; LIGANDS; DONORS; CHAIN in [Verma, Nitish; Renata, Septila; Lin, Chun-Hung] Acad Sinica, Inst Biol Chem & Chem Biol & Mol Biophys, Taiwan Int Grad Program, Inst Biol Chem, Taipei 11529, Taiwan; [Verma, Nitish] Natl Tsing Hua Univ, Dept Chem, Hsinchu 300044, Taiwan; [Tu, Zhijay; Liu, Shih-Hao; Ghosh, Bhaswati] Acad Sinica, Inst Biol Chem, Taipei 11529, Taiwan; [Lu, Ming-Shiuan; Phang, Riping; Lin, Chun-Hung] Natl Taiwan Univ, Dept Chem, Taipei 10617, Taiwan; [Renata, Septila] Natl Tsing Hua Univ, Coll Life Sci, Inst Bioinformat & Struct Biol, Hsinchu 300044, Taiwan; [Liu, Peng-Kai; Lin, Chun-Hung] Natl Taiwan Univ, Coll Life Sci, Inst Biochem Sci, Taipei 10617, Taiwan in 2021, Cited 34. Category: isothiazole. The Name is Benzoic anhydride. Through research, I have a further understanding and discovery of 93-97-0
Synthesis of type I LacNAc (Gal beta 1 -> 3GlcNAc) oligosaccharides usually suffers from low yields. We herein report the efficient synthesis of type I LacNAc oligosaccharides by chemoselective glycosylation. With 16 relative reactivity values (RRVs) measured thiotoluenyl-linked disaccharide donors and acceptors, chemoselective glycosylations were investigated to obtain optimal conditions. In these reactions, the RRV difference between the donors and acceptors had to be more than 6311 to obtain type I LacNAc tetrasaccharides in 72-86% yields, with minimal occurrence of aglycon transfer. The threshold of RRV difference was further applied to plan the synthesis of longer glycans. Because it is challenging to measure the RRVs of tetrasaccharides, anomeric proton chemical shifts were utilized to predict the corresponding RRVs, which consequently explained the outcome of glycosylations for the synthesis of type I LacNAc hexasaccharides. The result supported the idea that elongation of glycan chains has to proceed from the reducing to the nonreducing end for a better yield.
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Reference:
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